Best Apartments in Chestertown, MD for Your Vacation from $138

An aerial view of a town with a river, buildings, and surrounding greenery.

Bundle & Save
Get more, spend less whenever you see Bundle & Save deals
OneKeyCash
Earn OneKeyCash on all your eligible bookings
Upfront pricing
We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Chestertown apartments

A house with a swimming pool, surrounded by a fence, and two red umbrellas.

1. First Floor Studio Apartment in Historic Chestertown

Chestertown

John R.

$136 nightly

Nov 16 - Nov 17

Total with taxes and fees

A spacious living area with a dining table, sofa, and a kitchen in the background.

2. Newly restored apartment in the heart of Chestertown

Chestertown

Susan A.

$303 nightly

Nov 15 - Nov 16

Total with taxes and fees

A person sitting on a wooden deck by a calm body of water, surrounded by greenery.

3. Guest Suite for up to 2 in a Victorian on the Chester River

Millington

Quinton

$110 nightly

Nov 18 - Nov 19

Total with taxes and fees

A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

4. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Rock Hall

lisa p.

$264 nightly

Nov 21 - Nov 22

Total with taxes and fees

An aerial view of a property with a large house surrounded by lush greenery, a driveway, and a road nearby.

5. Turtle Cove Room

Kent County

Jennifer M.

$176 nightly

Nov 23 - Nov 24

Total with taxes and fees

A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

6. Beachcomber Suite

Kent County

"We absolutely loved staying at the Beachcomber Suite. Tucked away off the main road, with a massive screened porch to enjoy the country side and gardens. It was cosy, clean, well appointed. The shower was amazing. We had a multi-course dinner at Sassafras on the water which was right up the road, 3 minutes away on the water front. I got a text from Jane and Dennis that evening if I wanted fresh bagels in the morning. Well, of course I do! They were warm multi seed and fantastic start to...

Lisa E.

$189 nightly

Nov 23 - Nov 24

Total with taxes and fees

A fire pit with flames, surrounded by a metal frame, overlooking a body of water with a dock and trees in the background.

7. WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL

Aberdeen

Andy W.

$130 nightly

Nov 16 - Nov 17

Total with taxes and fees

A beach with a wooden pier extending into calm waters, surrounded by greenery and a clear sky.

8. Pool Loft Suite | Bay Access & Beach Passes

Cape Saint Claire

Ana S.

$405 nightly

Nov 15 - Nov 16

Total with taxes and fees

A white door with a frosted glass window, a wreath, and a framed inspirational quote.

9. Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals

Nottingham City

Linda M.

$215 nightly

Nov 17 - Nov 18

Total with taxes and fees

A waterfront with docked boats, a water taxi, and historic buildings.

10. Cozy Fells Point Gem / In The Heart of Fells Point

Fells Point

Carol

$186 nightly

Nov 17 - Nov 18

Total with taxes and fees

A modern living room with a sofa, a television mounted on the wall, and a fireplace.

11. Crown Suite Slps 7 2 Full BR Wd Floor Free ST Prk

Berea

$249 nightly

Nov 23 - Nov 24

Total with taxes and fees

A modern living room with a glass coffee table, a sofa, and a bookshelf. There is a staircase leading to an upper level.

12. Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC

Greektown

Rosa E.

$206 nightly

Nov 17 - Nov 18

Total with taxes and fees

A white building with black shutters, a wooden door, and a number '53' on the wall.

13. 18th Cent. Charm in Historic Downtown Annapolis

Historic District

Bradford R.

$354 nightly

Nov 15 - Nov 16

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Apartments

Cottages

Save an average of 15% on thousands of hotels when you're signed in

Top Chestertown Hotel Reviews

Hampton Inn Baltimore/White Marsh

10/10 Excellent

"Great stay, Nice and quiet."

Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

10/10 Excellent

"I booked 4 rooms for myself and my associates, and all of us were more than happy with the cleanliness of our rooms, great location and Neil was very accomodating giving us an early check-in and late check-out, which saved us precious time when getting to our destination. The surrounding area is also very nice with plenty of walkable places to eat, get snacks, etc. Only things I would say could use room for improvement is the bathroom door was a sliding door and a bit harder to engage, and the shower door kinda closes on it's own, which can be annoying for people who like steam showers. Other than that very nice stay and one I would recommend to colleagues."

Find out more about Chestertown

Chestertown Apartments information

Number of reviews	446
Accommodation	74 Apartments
Lowest Price	$138
Highest Price	$461

Frequently asked questions

What's it like to stay at an apartment in Chestertown?

You can choose from 5 apartments in Chestertown for your vacation.

Why should you consider apartments instead of traditional hotels?

An apartment comes equipped with a kitchen, so you can cook some of your meals, and usually is more spacious than a traditional hotel room. Apartments are a good option for solo travelers who want to live like locals, and also for families wanting the conveniences of home.

What's the top apartment for my stay in Chestertown?

Here are some of the more popular apartments in the area to choose from: First Floor Studio Apartment in Historic Chestertown: Includes a private pool, free WiFi, and private patios. A fitness center and onsite laundry facilities are on site. WORLD'S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD: Located 16.1 mi/25.9 km away in Earleville. Free WiFi and Smart TVs are included. WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL: Located in Aberdeen, 18.4 mi/29.5 km away. Includes free WiFi, private patios, and Smart TVs. Onsite laundry facilities and a hot tub are on site. Cozy Fells Point Gem / In The Heart of Fells Point: It's located in Baltimore, 28.3 mi/45.5 km from Chestertown. Includes free WiFi and Smart TVs.

How many apartments can I expect to find in Chestertown?

Expedia has 5 apartments to book in Chestertown.

What can I expect from the weather during my trip to Chestertown?

Weather is only one factor, but it can really affect your travel plans, especially when you're planning an extended stay in Chestertown. The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.

What should I see and do in Chestertown?

Cultural attractions include Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater, whereas Northern Chesapeake Bay and Chesapeake Bay are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Chestertown Historic District and Rolphs Wharf Marina.

What's the best way to get to and around Chestertown?

Knowing a bit about the transportation options can make your trip smoother when you get to your destination. Fly into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) from the heart of the city. Otherwise, you can search for flights to Easton, MD (ESN-Easton - Newnam), which is 28.2 mi (45.3 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.

Explore a world of travel with Expedia

Things to do in Annapolis

Room 1

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Chestertown apartments

1. First Floor Studio Apartment in Historic Chestertown

2. Newly restored apartment in the heart of Chestertown

3. Guest Suite for up to 2 in a Victorian on the Chester River